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View PropertiesAs of Apr, 27 2026
Highland Park, IL is a compact short-term rental market on Chicago's affluent North Shore with just 20 active Airbnb listings. The market generates an average annual revenue of $45,772 per listing, with a strong summer season that pushes monthly earnings above $6,000 in July and August. While the average daily rate of $269 falls below the Illinois state average of $319 and occupancy sits at 30% versus 33% statewide, the limited supply could present an opportunity for well-positioned properties to capture outsized demand during peak months.
According to Rabbu market data, the Highland Park short-term rental market shows:
| Metric | Context | Value |
|---|---|---|
| Active Airbnb Listings | As of Apr, 27 2026 | 20 |
| Average Daily Rate (ADR) | vs. $319 state avg. | $269 |
| Average Occupancy Rate | vs. 33% state avg. | 30% |
| RevPAN | ADR * Occupancy Rate | $81 |
| Average Monthly Revenue | Historical 12-month average | $3,814 |
| Average Annual Revenue | Historical 12-month average | $45,772 |
Data sources: Rabbu proprietary analytics as of Apr, 27 2026.
Highland Park's extremely low listing count and affluent suburban setting create a niche opportunity for investors willing to cater to seasonal North Shore demand.
Key investment factors
"Highland Park presents a niche, seasonal STR opportunity rather than a year-round cash-flow engine. Revenue swings dramatically from a low of roughly $1,965 in February to a peak of $6,118 in July — a spread of more than 3x — so investors need to budget for lean winter months. With only 20 active listings, the market is undersupplied, which can benefit operators who deliver a polished guest experience during the high-demand summer window. The overall opportunity is moderate: returns depend heavily on seasonal execution and keeping occupancy above the current 30% average through smart pricing and amenity investment."
— Rabbu Market Analysis Team
Highland Park's revenue cycle is sharply seasonal: July leads at $6,118 per listing and August nearly matches at $6,040, while February bottoms out at $1,965 — a 3:1 peak-to-trough ratio. The May–September window accounts for the lion's share of annual income, making summer marketing and pricing strategy critical for maximizing returns.
| Month | Trend | Revenue |
|---|---|---|
| January |
|
$2,122 |
| February |
|
$1,965 |
| March |
|
$2,749 |
| April |
|
$2,958 |
| May |
|
$4,245 |
| June |
|
$5,370 |
| July |
|
$6,118 |
| August |
|
$6,040 |
| September |
|
$4,572 |
| October |
|
$3,757 |
| November |
|
$3,135 |
| December |
|
$2,736 |
The available data shows 9 one-bedroom listings, accounting for a significant portion of the 20 total active listings. The remaining inventory likely includes larger properties, suggesting potential opportunity for investors targeting 2+ bedroom homes in an underrepresented segment of the market.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
9 |
One-bedroom properties in Highland Park command an ADR of $129, well below the overall market average of $269. This gap indicates that larger properties in the market are driving significantly higher nightly rates, making multi-bedroom homes the likely sweet spot for revenue-focused investors.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$129 |
One-bedroom listings generate a RevPAN of $43, compared to the market-wide average of $81. The disparity reinforces that larger properties are delivering substantially better revenue per available night, likely due to both higher ADR and stronger demand from families and groups visiting the North Shore.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$43 |
One-bedroom properties achieve a 34% occupancy rate, actually outpacing the market-wide average of 30%. While this suggests smaller units stay booked more consistently, their lower nightly rates mean the occupancy advantage doesn't translate into higher overall revenue.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
34% |
One-bedroom listings average $1,998 per month, roughly half of the market-wide average of $3,814. Investors targeting stronger monthly cash flow should consider larger property configurations that appear to be driving the market's higher revenue figures.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$1,998 |
At $23,978 per year, one-bedroom properties generate roughly 52% of the market-wide annual average of $45,772. This underscores that multi-bedroom properties in Highland Park are likely the higher-return play, though they also come with greater acquisition and operating costs.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$23,978 |
Kitchen and parking are universal at 100% of listings, reflecting guest expectations in this suburban market. Laundry facilities, self check-in, and a dedicated workspace each appear in 85% of listings, while outdoor amenities like backyards (75%) and outdoor furniture (70%) signal that guests value private outdoor space — a differentiator investors should prioritize.
| Amenity | Trend | Value |
|---|---|---|
| Kitchen |
|
100% |
| Parking |
|
100% |
| Dryer |
|
85% |
| Self Check-in |
|
85% |
| Washer |
|
85% |
| Workspace |
|
85% |
| Backyard |
|
75% |
| Outdoor Furniture |
|
70% |
| Patio or Balcony |
|
60% |
| Pets |
|
60% |
| BBQ Grill |
|
25% |
| Lake Access |
|
10% |
| Gym |
|
5% |
| Pool |
|
5% |
Understanding local STR regulations is essential before investing in Highland Park. Here's the current regulatory landscape:
Short-term rental operators in Highland Park, Illinois may be required to obtain a permit or register their property with the city before hosting guests. Investors should verify current requirements directly with Highland Park's municipal offices or the City of Highland Park website, as local STR regulations can change.
Common restrictions in Illinois municipalities can include limits on the number of occupants per property, minimum stay requirements, noise and nuisance ordinances, designated parking mandates, and caps on the number of permits issued. HOA rules may impose additional limitations, so investors should review any applicable homeowners' association covenants before purchasing.
Short-term rental hosts in Illinois are generally subject to state and local occupancy taxes, and in some cases sales or tourism-related taxes. Major booking platforms like Airbnb often collect and remit certain taxes on behalf of hosts, but operators should confirm their full tax obligations with a local tax professional.
Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Highland Park can provide current regulatory guidance.
Financing an Airbnb investment in Highland Park requires lenders who understand STR income. Rabbu partner lenders offer:
"Over the next 12–18 months, Highland Park's STR market is likely to remain heavily seasonal, with summer months continuing to drive the bulk of annual revenue. Investors can expect ADR to hold steady or edge up modestly in the $265–$280 range as limited supply constrains competition. Occupancy may see slight improvement if new listings don't flood the market, though winter months will likely remain soft with revenues in the $1,965–$2,750 range. Pairing a quality listing with strong amenities and competitive pricing should help outperform the current market averages."
— Rabbu Market Analysis Team
Rabbu provides Airbnb and short-term rental market data and statistics across the United States. Our mission is to empower investors with accurate insights and easy-to-use tools, so they can confidently identify and act on the best opportunities in the Airbnb market.
Rabbu proprietary analytics as of Apr, 27 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month historical averages and may not capture recent regulatory or market changes. Individual property results will vary based on location, quality, pricing strategy, and operational management.
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